Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

Li, Min; Li, Jia; Guo, Baodang; Liu, Xuanzhong; Yuan, Zhenbo; Wu, Yuehui; Yin, Huimin; Huang, Shuping; Zhang, Yan; Rao, Yijian

doi:10.1016/j.jcat.2021.05.003

Cited by 6 publications

(12 citation statements)

References 59 publications

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“…For the dual catalytic combination of Ni and Ir catalysts for the alkoxylation of aryl halides, the redox potential for E 1/2 red Ni(III)/Ni(II)=+0.71 V vs Ag/AgCl is within range of the measured E red HARCP*/HARCP ⋅− =+0.87 V vs SCE, purporting that ET from HARCP* and Ni(II) is feasible. Analogously, the redox potential for the Ir catalyst E 1/2 red Ir(III)/Ir(II)=−1.37 V is within range of that of HARCP, E 1/2 red HARCP/HARCP ⋅− =−1.43 V vs SCE, indicating that ET from HARCP ⋅− to Ni(III) is also likely [52] . These correlated values could warrant that the alkoxylation of aryl halides with photocatalyst HARCP could take place efficiently under the dual HARCP/Ni catalysis.…”

Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 66%

“…Li, Rao and colleagues [52] have also studied the alkoxylation of aryl halides employing HARCP as photocatalyst.…”

Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 99%

“…If instead of alcohol, water (40 equiv.) is used in the reaction, the respective alcohols can be synthesized under analogous reaction conditions [52] …”

Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 99%

“…Li, Rao and colleagues [52] utilized a synthetic derivative of Cercosporin (CP), namely HARCP (Scheme 16), for the photoreduction of aryl halides. Synthetic derivative HARCP has improved redox properties with respect to CP (for instance, while E 1/2 red CP/CP ⋅− =−0.46 V vs SCE, E 1/2 red HARCP/HARCP ⋅− =−1.43 V vs SCE) [52] .…”

Section: Reduction Reactionsmentioning

confidence: 99%

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Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

2022

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Due to the necessity for more environmentally benign processes in synthetic organic chemistry, and in particular in photocatalysis, a recourse to photocatalysts that are also found in nature and mimic natural processes to accomplish organic transformations is very appealing. Synthetic useful reactions such as oxidations, reductions, carbon-oxygen, carbon-carbon and carbon-sulfur bond formation reactions, and E-to-Z geo-metrical isomerization reactions photocatalyzed by biological natural pigments, vitamins, cofactors, and compounds with antiviral activity will be discussed in this account. Interestingly, due to the remarkable redox properties and triplet energies of some of these catalysts that are found in nature, both electron transfer (ET)-and energy transfer (EnT)-driven photocatalytic processes can be accomplished.

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Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 66%

“…Li, Rao and colleagues [52] have also studied the alkoxylation of aryl halides employing HARCP as photocatalyst.…”

Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 99%

“…If instead of alcohol, water (40 equiv.) is used in the reaction, the respective alcohols can be synthesized under analogous reaction conditions [52] …”

Section: Formation Of C−o Bonds Through Coupling Reactionsmentioning

confidence: 99%

Section: Reduction Reactionsmentioning

confidence: 99%

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Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

2022

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“…For example, according to the principle of structure–property relationship, Huang developed a new type of organic perylene photoreductant, hexacetyl-reduced cercosporin (HARCP). HARCP* was produced when HARCP was excited by visible light, and then reduced aryl bromine and activated aryl chloride compounds through photoinduced electron donors to construct aryl hydrides and aryl phenols under mild conditions [ 42 ] ( Figure 10 ). In addition, carbazolyl cyanophenyl (5CzBN) ( Figure 9 b) [ 43 ] could reduce activated aryl chloride to aryl hydride through photoinduced electron donor under visible light irradiation.…”

Section: Visible-light-driven Reduction Of Aryl Halides With Organic ...mentioning

confidence: 99%

Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals

et al. 2022

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Aryl- and heteroaryl units are present in a wide variety of natural products, pharmaceuticals, and functional materials. The method for reduction of aryl halides with ubiquitous distribution is highly sought after for late-stage construction of various aromatic compounds. The visible-light-driven reduction of aryl halides to aryl radicals by electron transfer provides an efficient, simple, and environmentally friendly method for the construction of aromatic compounds. This review summarizes the recent progress in the generation of aryl radicals by visible-light-driven reduction of aryl halides with metal complexes, organic compounds, semiconductors as catalysts, and alkali-assisted reaction system. The ability and mechanism of reduction of aromatic halides in various visible light induced systems are summarized, intending to illustrate a comprehensive introduction of this research topic to the readers.

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Biosynthesis of Natural and Unnatural Perylenequinones for Drug Development

Su,

Zhang,

Yuan

et al. 2024

ChemMedChem

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A wide range of perylenequinones (PQs) with diverse structures and versatile bioactivities have long been isolated, positioning them as highly promising agents for photodynamic therapy (PDT). However, the lack of an efficient and cost‐effective method to obtain these compounds and to introduce structural diversity and complexity currently hinders their further research and application. In this concept, we present a comprehensive overview of the advancements in the biosynthetic pathways of natural PQs based on their structural classification, and also summarize recent progress in the biosynthesis of natural PQs and derivatives. These pioneering efforts may pave the way for structure modification and large‐scale bioproduction of natural and unnatural PQs through synthetic biology strategies to promote their drug development.

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Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

Cited by 6 publications

References 59 publications

Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

Bioinspired Photocatalyzed Organic Synthetic Transformations. The Use of Natural Pigments and Vitamins in Photocatalysis

Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals

Biosynthesis of Natural and Unnatural Perylenequinones for Drug Development

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